1-Chloro-4-(chloromethyl)benzene → HCID 19771306, compound

HRID 1589921Notes

Reaction equation

HRID 1589921 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[Mg].[CH3:11][C:12]1([CH3:19])[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[CH:13]1>C(OCC)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:15]2([OH:18])[CH2:16][CH2:17][C:12]([CH3:19])([CH3:11])[CH:13]=[CH:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-HCID 5462224Magnesium

Product 1

HCID 19771306HCID 19771306, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 4-chlorobenzyl chloride (266 g, 1.65 mol) in diethyl ether (200 ml) was added slowly to a stirred mixture of magnesium (42 g, 1.73 mol) in diethyl ether (700 ml) to maintain the mixture at reflux. The mixture was warmed for a further 20 minutes after addition was complete. A solution of 4,4-dimethylcyclohex-2-en-1-one (226 g, 1.82 mol) in diethyl ether (60 ml) was then added dropwise over a period of 30 minutes so as to maintain the mixture at reflux and the mixture stirred overnight. The mixture was then quenched with water (250 ml) and hydrochloric acid (5M, 500 ml), extracted with diethyl ether (3×400 ml), backwashed once with sodium bicarbonate solution (5%w/v) and once with water and then dried with anhydrous magnesium sulphate. The solvent was then flashed off to give 369 g 1-(4-chlorobenzyl) -4,4-dimethylcyclohex-2-en-1-ol as an oil. NMR (in CDCl3 solvent, tetramethylsilane as reference) Characteristic peaks at:

Workup

  1. temperatureto maintain the mixture
  2. temperatureat reflux
  3. temperatureThe mixture was warmed for a further 20 minutes
  4. additionafter addition
  5. temperatureto maintain the mixture
  6. temperatureat reflux
  7. customThe mixture was then quenched with water (250 ml) and hydrochloric acid (5M, 500 ml)
  8. extractionextracted with diethyl ether (3×400 ml)
  9. dry with materialdried with anhydrous magnesium sulphate

Sources & evidence

ORD record
ord-82adacf5c70d417b8cd5914bf2f589ea
Source dataset
uspto-grants-1993_04
Patent number
US05200535

Reaction notes

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